Bromotrifluoromethane → 2-(Trifluoromethylthio)biphenyl

HRID 974066

반응식

HRID 974066 반응식
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Na+].[F:16][C:17](Br)([F:19])[F:18]>CN(C)C=O>[F:16][C:17]([F:19])([F:18])[S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 6384Bromotrifluoromethane3회HCID 24758Sodium hydrideHCID 27604132-Phenylthiophenol

생성물 1

HCID 109230652-(Trifluoromethylthio)biphenyl수율 87.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A reaction tube in a photoreaction apparatus was charged with 50 ml of dimethylformamide (DMF) and 5.59 g (30 mmol) of 2-mercaptobiphenyl, and with ice cooling and stirring, 1.2 g (30 mmol) of sodium hydride (60% in oil) was added. When foaming ceased, trifluoromethyl bromide was introduced into the reaction solution. The atmosphere within the reaction system was replaced by gaseous trifluoromethyl bromide, and while irradiating light from a high-pressure mercury lamp, about 2 equivalents of trifluoromethyl bromide was passed into the reaction system over about 2 hours. Ice water (150 ml) was added to the resulting brown reaction solution, and it was extracted with pentane. The organic layer was washed with water and then with saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The anhydrous magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give 6.71 g (87.9%) of 2-(trifluoromethylthio)biphenyl as an oil. It was purified by silica gel column chromatography. The properties of the product were as shown below.

후처리

  1. customwhile irradiating light from a high-pressure mercury lamp
  2. extractionwas extracted with pentane
  3. washThe organic layer was washed with water
  4. dry with materialwith saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  5. customThe anhydrous magnesium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-edb37228608e4725b18afee3f1e45907
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05066795

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